1: 93 percent / NaIO4 / methanol; H2O / 1.5 h / 0 °C 2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 15 min, 2) THF, hexane, -78 deg C, 30 min 3: 1) SOCl2, pyridine, 2) LiAlH4 / 1) THF, -10 deg C, 45 min, 2) THF, RT, 15 min then reflux, 30 min View Scheme

sodium tetrahydroborate; sodium periodate 1) MeOH, 1 h, 5 deg C, 2) MeOH, 0.5 h; Yield given. Multistep reaction;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11460447', constants.ctx, '0')">lithium aluminium tetrahydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />1&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 87 percent / K₂CO₃ / acetone / Heating<br />2: LiAlH₄ / tetrahydrofuran / 1 h / Heating<br /> <br /> &nbsp;